This study focuses on the phenomenon of private supplementary tutoring, otherwise known as 'shadow education', which has proliferated around the world. By casting the spotlight on one particular shadow education institution (SEI) in Singapore and viewing it through the lens of Dewey's educational philosophy, the study aimed to illuminate the inner workings of a SEI to shed light on its ability to thrive in a competitive educational landscape. Data were drawn from lesson observations, interviews with various stakeholders and the SEI website. Viewed through Dewey's philosophical thinking about the connections between the child and curriculum and school and society, the data shows an institution outwardly guided by a progressivist mission to develop learners as a whole, providing opportunities for broadening their minds and preparing them for their future workplace. However, evidence also suggests that there is a fundamental focus on high-stakes examination preparation in its pedagogic practices and curricular content. This tension reflects the wider socio-economic culture in Singapore that is entrenched within a utilitarian and pragmatic paradigm while aspiring towards more humanistic and holistic educational goals.